The 8 Best Weekender Bags of 2019

Pack your bags and hit the road

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A good weekend bag should be able to accommodate enough belongings for a two- to four-day trip without being too bulky. It should also be easy to haul — whether by wheels that can glide over cobblestonestone streets, or a shoulder strap that won't dig in when you’re schlepping to your hotel. Of course, a great weekend bag is also stylish — be it clean canvas, faux leather, or emblazoned with a cheeky saying. Whether you’re looking for a rough-and-ready duffel that can hold up to off-the-grid adventures or a sleek rolling suitcase for mini city breaks, we've got options.

Our Top Picks

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Best Overall: Away The Everywhere Bag

Leave it to Instagram’s favorite luggage brand — Away — to deliver an oh-so-sleek carryall for short-term travelers. The Everywhere bag is perfectly suited to a two- or three-day trip with six interior pockets (including one for a laptop), a hidden exterior pocket for your iPhone, and a zippered pocket for your umbrella. It’s also water- and abrasion-resistant thanks to its nylon construction, so your clothes will stay dry should the heavens open up as you step out of your cab. The bag is available in black, navy, and a sophisticated olive green, but you can also opt for a pebbled leather version in black or blush. Best of all, if you already own one (or two) of Away’s rolling suitcases, this bag is designed to slip right over the handle for easy toting. The Everywhere measures 6.3 x 7.3 x 10.2 inches and offers 20 liters of packing space.

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Best Budget: Sole Society Mason Weekend Bag

Authentic leather bags can run you an arm and a leg. If you'd rather go with a budget bag in order to put the bulk of your funds toward on-the-road experiences, this faux-leather option — which comes in under $100 — is one to consider. Sole Society's Mason Weekend Bag is chic, ultra-affordable, and roomy with a 19.5 x 12 x 10-inch build. Two carry handles and an adjustable shoulder strap make it easy to carry, while metal feet keep the bottom of your bag protected anytime you have to put it down on the sidewalk, subway, or mall floor. One of our favorite features is the zippered shoe compartment on the bottom, so you don't have to mix dirty sneaks with fresh tees and toothbrushes. The interior of the bag also offers a smartphone pocket so you don't have to dig around in the depths of your duffel when you hear your text tone. The tote is available in various neutral tones, from cognac and buttercream to gravel and pebbled black.

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Best Canvas: Cuyana Classic Weekender Bag

Cuyana makes some quality leather goods, but their canvas take on a weekender is just as covetable. Handcrafted in Turkey (so it will already have taken its first flight by the time it gets to you), the roomy bag is made from heavy-duty canvas — one of the most durable and forgiving fabrics out there — and features Italian leather detailing. In terms of design, there’s a zipper pocket and side pocket on the inside, plus two exterior side pockets you can easily slip your Kindle and wallet into for easy access. If your bag happens to pick up some dirt while on the go, just wipe it clean with a damp cloth. Color options range from two-tone gray and blush to sleek navy blue; Cuyana can also add a personalized monogram.

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Best Camp-Style: Herschel Supply Co. Sutton Mid-Volume Duffel

We love every retro detail of Herschel Supply Co.'s duffel, from the classic round shape and strap stitching to the gorgeously cross-hatched fabric and peek-a-boo signature striped lining. As far as organization goes, there’s a storage sleeve on the front that’s just the right size for tablets and everyday essentials you want to keep close at hand. The straps are well-designed too, with a dual handle to carry close to your shoulder and a longer strap for cross-body use. The Sutton Mid-Volume Duffel has more than enough room for a few days’-worth of clothing, and when you're not traveling, it also makes for a great gym bag. The bag measures 10.25 x 20.25 x 10.25 inches and weighs just a pound. You can pick one up in olive, glacier, kelp, pink, or painted floral.

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Best Cheeky Duffel: band.do Getaway Duffel Bag

ban.do products are practically synonymous with bright colors and pretty patterns, and this weekender is no exception. With an affordable price tag and size — 12.5 x 21.5 x 12.5 inches — that's domestic-airline-friendly, the Getaway Duffel is ideal for any two- to five-day getaways you may have on the books. An inside pocket keeps important valuables like tablets, passports, and wallets safe, and soft-sided canvas construction means you can easily fold it up and stow it away when not in use. If you don’t love the saying pictured, it also comes in a slew of other Instagram-approved patterns from primary-colored plaid to dainty florals.

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Best Rolling Duffel: Bric's X-Bag 21" Rolling Duffel

Sometimes you want a rolling bag — the better for sprinting through airports and, perhaps, coming home with more than you packed. Sometimes you want the ease and close-to-the-body carry of a duffel. Behold, the best of both worlds: Bric’s durable 21-inch rolling duffel. The bag's classic styling is reminiscent of a cool-kid dopp kit and it's lightweight at just 5.5 pounds. One word of warning: The bag fits within domestic carry-on size limitations, but you’ll want to double check your airline's restrictions before attempting an international flight. Love the bag but need more storage capacity for your next trip? The brand also makes a 28-inch version.

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Best for Business Travel: Tumi Larkin Anderson Duffel

Once you go Tumi, you can never quite settle for anything less — at least that seems to be the theme with frequent flyers and travelers looking for durable, stylish luggage. There’s no doubt that the brand's pieces are investments, but the pricey bags hold up for the long haul. The brand’s Larkin duffel is crafted from a tightly woven technical fabric, reinforced with leather trim (the seams are always the first to go, after all), and has a large exterior pocket for laptops and keeping your passport handy. It’s also lined for extra durability and comes with Tumi Tracer, a proprietary baggage recovery service that’s totally free. Should your bag get lost en route to your weekend conference, the geotracker will help you reclaim it.

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Best Garment Bag: Hook & Albert Leather Garment Weekender Bag

If you routinely get frustrated by the fact that most garment bags are super-cumbersome, try this one on for size. Hook & Albert’s leather bag may look like your regular, run-of-the-mill weekender, but it unfolds to reveal itself as a garment bag in disguise. It’s made from real leather and comes with three external pockets; including a tablet-sized pouch with a zip that sits against the side of your body for extra security. It’s great for business trips or occasions when you need to pack a suit. Just unzip the sides to pack, and easily rezip it before heading out the door. Another thing to love? It folds super-flat for storage once you’re back home and unpacked.